Is there a Python package or database source which would allow me to go from various romanizations of Arabic town names in Syria and Iraq to a canonical romanization?

Here is an example where the left romanization is one kind used by a US Government record collection and the other appears in a Syrian government press release. The Government names seem to be more well known and look-upable than the names used by the Syrian Government. I would like to find a canonical reduction of the two into a single reliable name:

The value for the name tag will have the place's name in the local language that is usually used for common signs and is also often the lingua franca for that particular place.

But, and what you're looking for - many places will also have an additional name: tag that represents the town's name in that particular language, as shown in the above image. OpenStreetMap (OSM) is a crowdsourced dataset so there may be many places that do not have an English or canonical romanization; or there may be some places that you'd consider to be a small village but OpenStreetMap has it tagged as a city; there may even be towns that are missing.

If you're comfortable with python, I'd recommend using the overpass wrapper to fetch the data; or you could use the overpass tool that I mentioned above, export into geojson and then convert into postgis, a postgresql library that supports geospatial functions.